The Surprising Perks Of Having A Portfolio Career

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© olly / Adobe Stock

Alyson Garrido, Career Coach
Alyson Garrido, Career Coach447
Job Search and Career Advancement

To many people, a dream job remains just that — a dream. They are scared to pursue their ideal opportunity due to family obligations, money, imposter syndrome... the list goes on and on. Sometimes things aren’t ‘bad’ enough to make a change. You like your job, but still see another occupation sparkling in the distance. Is that occupation really out of reach? Why not go for it while keeping your current job? Could you have more than one dream job at the same time?

In a recent article in the Harvard Business Review, Kabir Sehgal talked about the benefits of pursuing four (yes, four!) careers. I know what you’re thinking; this is impossible and I’m going to stop reading right now. Stick around, though, because it might be right for you. The word ‘career’ can feel all encompassing. One career is enough to manage, how could you have, two, three or four? Simple — by using the term 'portfolio career.'

I started down the portfolio career path before realizing there was such an option. I have my own business as a Career Coach and I love working one-on-one with my clients. Being a coach brings me a tremendous amount of joy. It's also the career in which I spend the most of my time, earn the most money and with which I most closely identify.

When I left my last nine-to-five job and started my own business, however, I quickly realized that giving my clients the attention they deserve meant that I would have to hold far fewer than 40 one-hour sessions per week – even 25 clients are more than most coaches work with in any given week.

So, I’ve got this extra time, now what? I went back to a passion of mine that I had put on the back burner and started teaching English as a Second Language at a language school. I thrived being in front of the classroom and was also able to help people reach their goals of learning a new language.

In both roles, I felt isolated and craved collaboration. That’s when I started consulting at an outplacement firm that helps recently-laid off people look for work. There, I had an office and a team of people to call on if I had questions, or just wanted a lunch buddy. Going into that office was one of the few places where I had traditional coworkers and regular meetings. While it’s not obligatory to be in those kinds of meetings, I found that I actually wanted to go and was interested in the content and professional development it would provide.

Did I mention I teach spin classes, too? I loved being in group cycling classes at my local YMCA, so why not get certified, I thought. Now I’m the first person to raise my hand and teach that 6 a.m. class that’s so hard to cover. I thrive on the energy of my students and I get in my workout. It keeps me motivated, and I motivate others.

These roles have created a rewarding career for me and I find tremendous joy in the work I do. Don’t get me wrong, it’s a juggle, but for me it has never felt like a burden. Different jobs have different peaks and valleys, so it creates variety for me and, surprisingly, it allows me to have more control over my time. I don’t have to rely on any of these jobs and they don’t rely on me, so it ends up being that I select and am selected for opportunities where I can truly shine and provide the most value. Teaching kindergarteners? Nope. Conversation class with adults? You bet! Creating a training course about a new process? Not my bag. Leading a workshop about difficult conversations? Sign me up!

I pick and choose in a way I never could when working a typical job. The opportunities that have come and gone have played to my strengths. I believe that new opportunities continue to come my way because I truly enjoy what I’m doing and this love shines through — along with a healthy dose of hustle! All of the opportunities I described were earned through introductions from colleagues who saw the value I could provide. Networking is key if you’re thinking of pursuing a portfolio career.  

Anna Thomson, founder of Roar Fierce Craniosacral and Coaching, and I recently discussed this alternative career path. “I was described by one of my personal trainers as a hard worker — and I think you have to be to have a portfolio career,” Anna explained .“This isn't a ‘do nothing and get away with it’ choice. But I do get to make my schedule work with me rather than me work for my schedule. And I love that.” For her, a portfolio career also helps her expand her skill set. She describes having lots of tools in her "

For her, a portfolio career also helps her expand her skill set. She describes having lots of tools in her "kete" (bag of tricks) that can assist people. Anna appreciates having options to try if her clients are looking for a different approach.

A portfolio career could allow you to work in completely different areas at the same time. For me, it consistently sharpens my skills as I use them in different areas. For Anna, she is able to support her clients herself, rather than sending them to other professionals for the resources they need. With this type of career, you might be able to bring that side hustle more toward the center and see what it’s like to have the job that you’ve always considered to be out of your reach.


Alyson Garrido is passionate about helping women advance their careers and find jobs they will enjoy. As a career coach, she partners with her clients to identify their strengths and create a path toward a more fulfilling career. Alyson provides support around preparing for interviews, performance reviews and salary negotiations, ensuring that you present yourself in the best possible light for job search and career advancement. Learn more or book a session with Alyson by visiting